2,2,2-Trifluoro-3'-(trifluoromethyl)acetophenone → N-[2,2,2-Trifluoro-1-(3-(trifluoromethyl)phenyl)ethylidene]-N'-(2,4,6-triisopropylbenzenesulfonyl)hydrazine

Participants

Reaction Conditions

Reaction Steps

2,2,2-Trifluoro-3'-(trifluoromethyl)acetophenone (3.7 g, 0.15 mol) was dissolved in dichloromethane (15 ml, anhydrous) and the solution was cooled to 0° C. Titanium tetrachloride (15 ml, 1.0M in dichloromethane) was added to the solution dropwise and the resulting ochre suspension was stirred at room temperature for 12 h. 2,4,6-Triisopropylbenzenesulfonyl hydrazine (3.8 g, 0.015 mol) was added to the suspension and the reaction mixture was stirred for 2 h. The mixture was quenched with water and the organic phase was separated, washed with brine, dried and the solvent was removed in vacuo. The resulting solid was purified by column chromatography using 10-25% ethyl acetate in hexane as eluant. This afforded the product as a white crystalline solid (3.9 g). 1HNMR (250 MHz, CDCl3) δ 1.10-1.22 (m, 18H, (CH3)2), 2.86 (septet, 1H, C H(CH3)2), 4.02 (septet, 2H, C H(CH3)2), 7.14 (S, 2H, ArH), 7.40-7.48 (m, 2H, ArH), 7.64 (t, 1H, ArH), 7.72-7.80 (m, 1H, ArH), 8.72 (s, 1H, NH).

Provenance & Evidence